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[ CAS No. 158001-28-6 ] {[proInfo.proName]}

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Chemical Structure| 158001-28-6
Chemical Structure| 158001-28-6
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Product Details of [ 158001-28-6 ]

CAS No. :158001-28-6 MDL No. :MFCD00128289
Formula : C8H12N4 Boiling Point : -
Linear Structure Formula :- InChI Key :WXEIWFYQLJCWSP-UHFFFAOYSA-N
M.W : 164.21 Pubchem ID :2797454
Synonyms :

Calculated chemistry of [ 158001-28-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.5
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.91
TPSA : 67.63 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.55
Log Po/w (XLOGP3) : 1.05
Log Po/w (WLOGP) : 1.1
Log Po/w (MLOGP) : 0.26
Log Po/w (SILICOS-IT) : 0.21
Consensus Log Po/w : 0.83

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.76
Solubility : 2.84 mg/ml ; 0.0173 mol/l
Class : Very soluble
Log S (Ali) : -2.06
Solubility : 1.43 mg/ml ; 0.00869 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.34
Solubility : 7.54 mg/ml ; 0.0459 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.0

Safety of [ 158001-28-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 158001-28-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 158001-28-6 ]
  • Downstream synthetic route of [ 158001-28-6 ]

[ 158001-28-6 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 7400-27-3 ]
  • [ 123-06-8 ]
  • [ 158001-28-6 ]
YieldReaction ConditionsOperation in experiment
94%
Stage #1: With triethylamine In ethanol for 1 h;
Stage #2: at 80℃;
To a suspension of fe/ -butylhydrazine hydrochloride (15.0 g, 120.4 mmol) in ethanol (600 ml_) was added triethylamine (16.8 ml_, 120.4 mmol). The mixture was stirred for 60 min until the hydrazine had dissolved. Ethoxymethylenemalononitrile (14.7 g, 120.4 mmol) was added in portions and the reaction mixture was heated to 80 °C and stirred at this temperature overnight. The reaction mixture was concentrated to dryness and the obtained residue was taken up in EtOAc. The organic layer was washed with water, dried over Na2S04, filtered and concentrated under reduced pressure. The solid was then recrystallized in DCM to afford 5-amino-1 -fe/?-butyl-pyrazole-4-carbonitrile (18.6 g, 1 13.4 mmol, 94percent yield) as a light yellow solid. LC-MS (ES+, method 1): 1 .36 min, m/z 165.1 [M+H]+
83% With triethylamine In ethanol for 3 h; Reflux In tert-butylhydrazine hydrochloride (8.67 g, 69.6 mmol)Was added triethylamine (9.7 mL, 69.6 mmol)After adding anhydrous ethanol (460 mL), the mixture was stirred and dissolved at room temperature,Ethoxymethylenemalononitrile (8.5 g, 69.6 mmol) was added in small portions.After heating the solution to reflux for 3 hours,After cooling, the solvent was evaporated to give an orange solid.And extracted with ethyl acetate (0.5 L) and water (0.25 L)After drying by adding magnesium sulfate,The organic layer was evaporated to give an orange-yellow solid.The resulting solid was continuously washed with a 10percent ethyl acetate in cyclohexane solution to give a crystalline solid5-amino-1-tert-butyl hydrogen - pyrazol-4-cyano 9.54g(Yield: 83percent).
64.4% With triethylamine In ethanol for 3 h; Heating / reflux A mixture of t-butylhydrazine hydrochloride (4.67 g, 53 mmol) and triethylamine (5.35 g, 53 mmol) in anhydrous ethanol (250 ml) was stirred and ethoxymethylene malononitrile (6.47 g, 53 mmol) was slowly added in portions. The mixture was heated at reflux for 3 hr. The solvent was removed in vacuo and the product was crystallized from ethyl acetate -hexane followed by ether to afford the title compound as light pale brown crystals (5.6 g, 64.4 percent); LC/MS, API-ES, Neg, (M-H)", 163.0.
Reference: [1] MedChemComm, 2017, vol. 8, # 3, p. 640 - 646
[2] Patent: WO2017/46604, 2017, A1, . Location in patent: Paragraph 00228
[3] Organic Letters, 2012, vol. 14, # 15, p. 3906 - 3908
[4] Patent: CN106008527, 2016, A, . Location in patent: Paragraph 0048; 0049; 0050; 0051
[5] European Journal of Organic Chemistry, 2008, # 19, p. 3377 - 3381
[6] Patent: WO2007/126841, 2007, A2, . Location in patent: Page/Page column 73
[7] Patent: WO2009/62118, 2009, A2, . Location in patent: Page/Page column 170
[8] Patent: WO2017/161344, 2017, A1, . Location in patent: Paragraph 0813-814
[9] Journal of Medicinal Chemistry, 2017, vol. 60, # 24, p. 9976 - 9989
  • 2
  • [ 32064-67-8 ]
  • [ 123-06-8 ]
  • [ 158001-28-6 ]
YieldReaction ConditionsOperation in experiment
83% With triethylamine In ethanol at 100℃; for 0.5 h; Microwave irradiation To a mixture of t-butylhydrazine (1.0 g, 8.2 mmol) and triethylamine (1.1 ml, 8.2 mmol) in anhydrous ethanol (20 ml) was added ethoxymethylene malononitrile (7, 1.0 g, 8.2 mmol) slowly in portions. The mixture was heated in a microwave at 100 °C for 30 min. and then concentrated via evaporation of the solvent under a reduced pressure. The residue was washed with ether then dried under a reduced pressure. The product was isolated as a yellow solid in 83 percent yield (1.1 g, 6.7 mmol). 1H NMR (200 MHz, CDCl3): δ 7.37 (s, 1 H), 4.54 (s, 2 H), 1.58 (s, 9 H); 13C NMR (50 MHz, CDCl3): δ 150.1, 138.3, 114.7, 77.8, 59.9, 28.9; HRMS (CI) calcd for C8H12N4 (M) 164.1062, found 164.1080.
87% With sodium methylate In ethanol (a)
1-tert-Butyl-5-amino-1H-pyrazole-4-carbonitrile
To a mixture of tert-butylhydrazine (40 g, 0.32 mol), sodium methoxide (18 g, 0.32 mol) and ethanol 150 ml) was added ethoxymethylene malononitrile (42 g, 0.32 mol).
The reaction mixture was heated to reflux for 2 hours and the solvent was removed in vacuo.
The residue was extracted with chloroform, washed with water and the organic layer was concentrated in vacuo to afford 46 g (87percent) of 1-tert-butyl-5-amino-1H-pyrazole-4-carbonitrile as a semi-solid.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 44, p. 5761 - 5763
[2] Journal of Medicinal Chemistry, 1996, vol. 39, # 5, p. 1164 - 1171
[3] Patent: US5294612, 1994, A,
[4] Chemistry - A European Journal, 2018,
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